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Biggest problem with batch files is error-checking and error recording.

For example, if your outlook mailbox is locked, does the backup fail or just flash up a little error message for a fraction of a second.
You could end up with lots of backups, but all missing the file you want to restore.

Since you mention Jungle Disk, does it not allow you to backup the files automatically?

If you create large zip files (especially if they are compressed/encrypted) and attempt to upload them, it may very much harder on your bandwidth than backing up files individually.

It allows uploading. The problem is about security. I want to have a really secure container. Basically RackSpace uses 64bit encryption which is almost nothing. Amazon uses 256bit, much better, but you still entrust your password to 3rd party. I want to have a space which only I can open, no one else. So basically I want to give enough protection for those docs. Mail client backup is not really important.. his mails are on the servers.
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ShikiJul 19 '10 at 18:02

By the way, there are command line parameters to allow you to mount and/or dismount a TrueCrypt volume, but when I tried it, one of the required options was the password (and the idea of putting the password in plain text batch file put me off).
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sgmooreJul 20 '10 at 17:54

Hey having the plain password in the batch is not a problem in my opinion. You store it on your PC, not on the backup space.
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ShikiJul 22 '10 at 8:32